Diacetoxyiodobenzene mediated oxidative dethionation of N-substituted-5-arylmethylidene rhodanines: an efficient synthesis of N-substituted-5-arylmethylidene thiazolidine-2,4-diones

A simple and efficient synthesis of N-substituted-5-arylmethylidene thiazolidine-2,4-diones has been developed via oxidative dethionation of N-substituted-5-arylmethylidene rhodanines using diacetoxyiodobenzene (DIB) in ethanol at room temperature. This protocol is simple, mild, column free, obviates the need of acids and bases, and offers a broad substrate scope. [GRAPHICS]